2008Helvetica Chimica ActaRequires access

Triumfettamide and Triumfettoside Ic, Two Ceramides and Other Secondary Metabolites from the Stems of WildTriumfetta cordifolia A. Rich . (Tiliaceae)

Louis P. Sandjo, Paul Hannewald, Mehdi Yemloul, Gilbert Kirsch, Bonaventure T. Ngadjui

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Abstract

Abstract Two new ceramides, triumfettamide (1) and triumfettoside Ic (2), characterized as (2R,6Z)‐2‐hydroxy‐N‐[(2S,3S,4R)‐1,3,4‐trihydroxyhexacosan‐2‐yl]heptadec‐6‐enamide and (2R)‐N‐{(1S,2R,3E,6Z, 9Z,12Z,15Z)‐1‐[(β‐D‐glucopyranosyloxy)methyl]‐2‐hydroxyheneicosa‐3,6,9,12,15‐pentaen‐1‐yl}‐2‐hydroxytetradecanamide, respectively, were isolated from the stems ofTriumfetta cordifoliaA. Rich.besides eight known secondary metabolites identified as heptadecanoic acid,β‐sitosterol glucopyranoside, friedelin, lupeol, betulin, maslinic acid, 2‐hydroxyoleanolic acid and the mixture of stigmasterol andβ‐sitosterol. Their structures were determined on the basis of spectroscopic methods as well as HR‐MALDI‐FT‐ICR‐MS analysis, chemical transformation, and by comparison of their physical and spectral data with those reported in the literature and with authentic specimens for some known compounds. Five pentacyclic triterpenoids, friedelin, lupeol, betulin, maslinic acid, and 2‐hydroxyoleanolic acid, have been isolated fromTriumfettagenus for the first time.

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Abstract Two new ceramides, triumfettamide (1) and triumfettoside Ic (2), characterized as (2R,6Z)‐2‐hydroxy‐N‐[(2S,3S,4R)‐1,3,4‐trihydroxyhexacosan‐2‐yl]heptadec‐6‐enamide and (2R)‐N‐{(1S,2R,3E,6Z, 9Z,12Z,15Z)‐1‐[(β‐D‐glucopyranosyloxy)methyl]‐2‐hydroxyheneicosa‐3,6,9,12,15‐pentaen‐1‐yl}‐2‐hydroxytetradecanamide, respectively, were isolated from the stems ofTriumfetta cordifoliaA. Rich.besides eight known secondary metabolites identified as heptadecanoic acid,β‐sitosterol glucopyranoside, friedelin, lupeol, betulin, maslinic acid, 2‐hydroxyoleanolic acid and the mixture of stigmasterol andβ‐sitosterol. Their structures were determined on the basis of spectroscopic methods as well as HR‐MALDI‐FT‐ICR‐MS analysis, chemical transformation, and by comparison of their physical and spectral data with those reported in the literature and with authentic specimens for some known compounds. Five pentacyclic triterpenoids, friedelin, lupeol, betulin, maslinic acid, and 2‐hydroxyoleanolic acid, have been isolated fromTriumfettagenus for the first time.

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Available abstract

Abstract Two new ceramides, triumfettamide (1) and triumfettoside Ic (2), characterized as (2R,6Z)‐2‐hydroxy‐N‐[(2S,3S,4R)‐1,3,4‐trihydroxyhexacosan‐2‐yl]heptadec‐6‐enamide and (2R)‐N‐{(1S,2R,3E,6Z, 9Z,12Z,15Z)‐1‐[(β‐D‐glucopyranosyloxy)methyl]‐2‐hydroxyheneicosa‐3,6,9,12,15‐pentaen‐1‐yl}‐2‐hydroxytetradecanamide, respectively, were isolated from the stems ofTriumfetta cordifoliaA. Rich.besides eight known secondary metabolites identified as heptadecanoic acid,β‐sitosterol glucopyranoside, friedelin, lupeol, betulin, maslinic acid, 2‐hydroxyoleanolic acid and the mixture of stigmasterol andβ‐sitosterol. Their structures were determined on the basis of spectroscopic methods as well as HR‐MALDI‐FT‐ICR‐MS analysis, chemical transformation, and by comparison of their physical and spectral data with those reported in the literature and with authentic specimens for some known compounds. Five pentacyclic triterpenoids, friedelin, lupeol, betulin, maslinic acid, and 2‐hydroxyoleanolic acid, have been isolated fromTriumfettagenus for the first time.

Key concepts: Friedelin, Lupeol, Chemistry, Betulin, Stigmasterol, Stereochemistry, Triterpenoid, Chromatography

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Triumfettamide and Triumfettoside Ic, Two Ceramides and Other Secondary Metabolites from the Stems of WildTriumfetta cordifolia A. Rich . (Tiliaceae) — Research Paper | ScholarLens